Plot
After a skateboarding lesson gone wrong, Lillie ends up knocking one of her baby teeth loose and is scared of just yanking it out. Leo tries to help much to the others dismay, claiming that Leo would end up 'scarring' Lillie for helping her with her baby tooth after the incident between him and Donnie as tots.

Leo and Lillie were on top of the half pipe as Leo had his signature skateboard and he had let Lillie use his old skateboard from when he was a tot as the boys were teaching Lillie how to skateboard.

The other brothers however were a bit more careful with teaching Lillie how to skateboard, Mikey, Donnie and Raph always made sure Lillie wore the proper safety gear when they taught her different tricks on skateboarding.

Lillie was wearing a blue skateboarding helmet and she looked at Leo with a bit of worry since she had never been on top of the half pipe before, she was a bit unsure if she was able to go down the half pipe.

Leo glanced at Lillie and he noticed her unease as he softly patted Lillie's helmet with a small smile. "Relax Lil's, you've got this. Besides, we made sure that you're prepared if you fall. Now, just do what I do okay?" Leo explained.

"Okay..!" Lillie nodded and held her board as Leo got on his skateboard and he skated down the half pipe to the other side to show Lillie what to do correctly and made up the other side of the half pipe, kicking up his board as he caught it and looked over at Lillie. "Now it's your turn Lillie!" Leo chimed.

Lillie gulped quietly but she looked down the half pipe and she shivered a little but shook off her fear as she then got on her skateboard once she got on the spot Leo was on, she then took a breath and skated down the half pipe as Leo kept an eye on her and Lillie gave a yelp as she almost lost balance on the board but managed to regain it. "You're doing great kiddo!" Leo said.

Lillie smiled a little and she tried to pick up enough speed to reach the other side but soon the board hit a bump in the half pipe, which launched Lillie off the board and hit the ground face first.

Leo's eyes widened and he got down from the half pipe as he ran over to Lillie and helped her back up onto her feet, he crouched next to her but he saw Lillie covering her mouth with her hands, whimpering softly. "Lil's what happened? Let me see!" Leo got worried that Lillie may have broken a tooth and the little girl shook her head no.

"What's going on in here?" Raph had got a bad feeling so he checked up on the two but soon saw Lillie covering her mouth, the snapper rushed over and it caught Donnie and Mikey's attention, making them peek from the kitchen as they went over to see what happened. "Lillie, what happened?" Raph asked.

"I'm guessing nardo happened." Donnie remarked, he crossed his arms and took notice of the skateboards as Leo looked at his twin. "It wasn't my fault!" Leo said.

"Then explain." Donnie said, he was wondering what exactly happened and he seemed puzzled why Lillie was covering her mouth like she was trying to hide something from them. "I was teaching Lillie how to go down and back up on the half pipe, the board hit something on the ramp and the kid went flying." Leo explained.

"And she hit the ground face first? Leo! She could have broken a tooth!" Raph said, Mikey went to Lillie and he pulled her aside as he calmed her down while Raph and Leo talked. "Lillie I know it hurts, but can you just let me take a look? We need to make sure that nothings broken." Mikey explained to her.

Lillie looked at the orange masked turtle but she nodded and she uncovered her mouth as she gave a whine, the pain kept hurting her and Donnie grabbed a pen light after he put on a face mask. "Okay Lillie, say ahh." Donnie said, Lillie opened her mouth just enough for them to see what happened as it turned out, one of Lillie's canines was knocked loose as it wiggled a bit in her mouth.

"Okay, false alarm gentlemen. None of Lillie's teeth are broken, but her left canine is knocked loose from the impact." Donnie said, he went over to Leo and Raph as Lillie closed her mouth.

"In English." Leo sighed, he crossed his arms over his chest as Donnie removed his face mask and he gave his twin a look. "It's a baby tooth, it was bound to come out anyway. So by hitting the ground with such impact, it knocked it loose but not completely." Donnie said.

"So Lillie is just losing her first baby tooth?" Raph asked, looking at Donnie who gave a nod and Mikey smiled a little while Lillie seemed more worried by the news, she had never handled losing a tooth before. "It's still in her mouth, so it can come out naturally." Donnie said.

"I don't wanna! What if it hurts?" Lillie protested, she gave a soft whine as she held her cheek and Mikey comforted Lillie to the best of his ability while Leo suggested that he could remove the tooth himself but he saw Donnie and Raph glare down at him.

"Absolutely not!" Donnie said, he was pretty defensive and Raph crossed his arms over his plastron while he looked at Leo. "I'm agreeing with Donnie on this, besides the last time you tried to take out a tooth it was Donnie's when we were tots. We all know how that went." Raph said.

"It's not my fault I removed his first upper bicuspid instead of his cracked second one!" Leo said, he looked at Raph and Donnie was still against the idea but Leo thought of a way to remove the tooth with much more ease.

"Look, what if I don't remove the tooth. Buut, we use some ideas I have to get it out?" Leo suggested, Mikey told Leo that none of the ideas can be harmful to Lillie and Leo understood as they started the first plan Leo had. Donnie helped out while Leo carefully tied a string around Lillie's loose tooth and he smiled a little.

"Okay, the string is secured!" Leo looked over at Donnie who was next to a door as Donnie gave a nod while Lillie was hugging onto Leo's arm, she looked scared. "Don't worry Lil's, it won't hurt. It'll be quick and painless. We'll go on three." Leo said.

"Okay.." Lillie mumbled, Leo counted down and once he got to three he signaled Donnie as Donnie shut the door and it pulled the string but the tooth didn't come out even with the amount of force from the door shutting as Lillie gave a small cry. "Make it stop!" Lillie cried.

"Okay, that didn't work." Donnie remarked, Leo cut the string and he calmed Lillie down as he tried to think of something else but soon he saw Lillie run off to hide. "Lillie wait!" Leo felt bad for Lillie and he sighed mentally while Donnie groaned quietly, he walked over to Leo and patted his shell softly.

"Just give her time, Lillie's probably never handled this before. We can't exactly rush her. Go and talk to her." Donnie said, he was surprisingly caring but in his own way as Leo glanced at Donnie but he gave a nod.

Donnie went to his lab to be alone while Leo decided to bring Lillie something as an apology after the fail with the string trick, Lillie was hiding in her room and she gave a quiet whine as she hid under her blankets while her loose tooth was still in pain but she eventually heard footsteps after a while.

"Lillie, can I come in?" Leo asked, he stood outside Lillie's room and he held a plate in his hands as Lillie stayed under her blankets but moved it slightly so Leo could hear her. "I guess." Lillie responded.

Leo walked into the room and he saw the blanket mountain Lillie made to hide under as he went over to the bed, Lillie peeked out of hiding while she looked at Leo. "I made apology apple bunnies.." Leo turned the plate to show Lillie the cute bunny shaped apple slices that he made and Lillie came out from under her blankets as she sat up and looked away.

"Look, Lil's. I'm sorry, I'm sorry that you had to be in that much pain. But I was just trying to help you get your baby tooth out." Leo said, he sighed a bit.

"But it still hurts Leo.." Lillie said, she pulled her legs to her chest and she looked at the ground as Leo put the plate of apple slices next to Lillie before he gave a soft sigh, leaning back a little. "I don't usually tell this to anyone, but the first time I lost a baby tooth, I freaked out. Just like you did." Leo said, Lillie perked up and she looked over at Leo.

"Yep, I was practically crying like a baby. Raph had to hold me still while Donnie shut the door with my tooth tied to a string, one swift pull and pop! The pain was done and over with. Loosing a baby tooth ain't all that bad Lil's, it just means your growing up." Leo explained.

Lillie thought to herself quietly but she seemed to understand as she let go of her legs and Leo ruffled her hair, Lillie giggled but she grabbed one of the bunny apple slices and bit into it but she immediately yelped and pulled it away. "Ouch..!" Lillie held her mouth but Leo noticed something as the two of them saw Lillie's baby tooth was stuck in the apple slice, it was out.

"Ha! It's out and I didn't even have to use the backup plan, does it hurt anymore Lillie?" Leo asked, turning to his little sister and Lillie uncovered her mouth as he saw Lillie smiled a little but was missing her baby tooth.

"Nope..! It feels a lot better now!" Lillie chimed, she smiled as then curiously asked what she was supposed to do with her baby tooth and Leo explained to her that she would get a visit from the tooth fairy tonight.

"And she's super sweet, she leaves money for kids who lose their baby teeth." Leo explained, Lillie got stars in her eyes but she understood as she got excited about tonight, planning to stay up to see the tooth fairy.

Timeskip

Late at night, Lillie was fast asleep in her bed and hugging her plush bunny, Mei. She couldn't stay awake long enough so she ended up sleeping, she gave a tired hum in response as she nuzzled her plushy and Lillie stayed asleep as the curtain to her room moved.

Leo peeked into the room and he used his ninja stealth to get into the room as he wore a sparkly pink tutu and fairy wings incase Lillie woke up and planned on seeing him.

"Okay.. easy." Leo whispered to himself, he carefully reached under the pillow and grabbed the tooth as he pulled it out from under the pillow while making sure that Lillie remained asleep. He then put the money under Lillie's pillow and he froze when Lillie turned in her sleep as Lillie gave a sleepy hum, turning over onto her side but stayed asleep.

Leo breathed a quiet sigh of relief and he snuck out of the room as he ended up bumping into Donnie, who was pulling an all nighter and Donnie held his mug of coffee while he looked at his twin with genuine confusion. "What in the pizza supreme in the sky are you wearing?" Donnie asked.

"Tooth fairy outfit, long story." Leo said, Donnie grabbed his phone and snapped a picture before returning to his lab as Leo groaned quietly in annoyance but went to his room as he was just glad to make Lillie happy after losing her first baby tooth.